All Cast

Owen Wilson

Owen Wilson

Dupree

Kate Hudson

Kate Hudson

Molly

Matt Dillon

Matt Dillon

Carl

Michael Douglas

Michael Douglas

Mr. Thompson

Seth Rogen

Seth Rogen

Neil

Amanda Detmer

Amanda Detmer

Annie

Ralph Ting

Ralph Ting

Toshi

Todd Stashwick

Todd Stashwick

Tony

Bill Hader

Bill Hader

Mark

Lance Armstrong

Lance Armstrong

Lance Armstrong

Jason Winer

Jason Winer

Eddie

Sidney S. Liufau

Sidney S. Liufau

Paco

Billy Gardell

Billy Gardell

Bartender Dave

Eli Vargas

Eli Vargas

Aaron

Houston Mack

Houston Mack

Dougie

Bob Larkin

Bob Larkin

Army Veteran

Suzanne Ford

Suzanne Ford

Thompson's Secretary

Claudia Choi

Claudia Choi

Carl's Secretary

Summer Altice

Summer Altice

Stripper

Jeanine Hass

Jeanine Hass

Stripper

Peter Ruocco

Peter Ruocco

Wedding Planner

Joe Russo

Joe Russo

Personnel Manager

Lance Irwin

Lance Irwin

Neighborhood Father

Fenessa Pineda

Fenessa Pineda

2nd Grade Girl

Mario Revolori

Mario Revolori

2nd Grade Boy

Jay Lembeck

Jay Lembeck

Minister

Gil Harris

Gil Harris

Reese

Pat Crawford Brown

Pat Crawford Brown

Aunt Kathy

Bayani Ison

Bayani Ison

Hawaiian Bartender

Joe Wilson

Joe Wilson

Joe

Blaine Pate

Blaine Pate

Larry

Kevin Breznahan

Kevin Breznahan

Charlie

Trevor Stock

Trevor Stock

Herb

Sean Perrone

Sean Perrone

Ned

Craig Hosking

Craig Hosking

Pilot

Harry Dean Stanton

Harry Dean Stanton

Curly (uncredited)

Amber Hay

Amber Hay

Wedding Guest (uncredited)

Kepa Kruse

Kepa Kruse

Waiter (uncredited)

Michelle Lee

Michelle Lee

Hawaiian Air Ticketing Agent (uncredited)

May Porter

May Porter

Waitress (uncredited)

Tasha Smith

Tasha Smith

Co-Worker (uncredited)